RU2005109156A - NEW COMPOUNDS - Google Patents

NEW COMPOUNDS Download PDF

Info

Publication number
RU2005109156A
RU2005109156A RU2005109156/04A RU2005109156A RU2005109156A RU 2005109156 A RU2005109156 A RU 2005109156A RU 2005109156/04 A RU2005109156/04 A RU 2005109156/04A RU 2005109156 A RU2005109156 A RU 2005109156A RU 2005109156 A RU2005109156 A RU 2005109156A
Authority
RU
Russia
Prior art keywords
alkyl
methyl
substituted
trifluoroethyl
carboxamide
Prior art date
Application number
RU2005109156/04A
Other languages
Russian (ru)
Other versions
RU2323211C2 (en
Inventor
Даниэль ПАЖЕ (CA)
Даниэль Паже
Кристофер УОЛПОЛ (CA)
Кристофер Уолпол
Хьюэй ЯНГ (CA)
Хьюэй ЯНГ
Original Assignee
Астразенека Аб (Se)
Астразенека Аб
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Астразенека Аб (Se), Астразенека Аб filed Critical Астразенека Аб (Se)
Publication of RU2005109156A publication Critical patent/RU2005109156A/en
Application granted granted Critical
Publication of RU2323211C2 publication Critical patent/RU2323211C2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Immunology (AREA)
  • Psychology (AREA)
  • Transplantation (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (18)

1. Соединение формулы (I) или его фармацевтически приемлемые соли:1. The compound of formula (I) or its pharmaceutically acceptable salts:
Figure 00000001
Figure 00000001
 где RF1 и RF2 независимо представляют собой электроноакцепторные группы;where R F1 and R F2 independently represent electron withdrawing groups; Z выбран из O= и S=;Z is selected from O = and S =; R1 выбран из С1-10алкила; C1-10алкила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; С2-10алкенила; С2-10алкенила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; С2-10алкинила; С2-10алкинила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; R3R4N-C1-6алкила; R3R4NC(=О)-C1-6алкила; R3О-С1-6алкила; R3OC(=O)-C1-6алкила; R3C(=O)-C1-6алкила; R3C(=O)NR3-C1-6алкила; R3R4NSO2-C1-6алкила; R3CSO2N(R4)-C1-6алкила; R3R4NC(=O)N(R5)-C1-6алкила; R3R4NSO2N(R5)-C1-6алкила; арил-С1-6алкила; арил-С(=O)-С1-6алкила; гетероциклил-С1-6алкила; гетероциклил-С(=O)-С1-6алкила; замещенного арил-С1-6алкила; замещенного арил-С(=O)-С1-6алкила; замещенного гетероциклил-С1-6алкила; замещенного гетероциклил-С(=O)-С1-6алкила и C1-10гидрокарбиламино;R 1 selected from C 1-10 alkyl; C 1-10 alkyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; C 2-10 alkenyl; C 2-10 alkenyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; C 2-10 alkynyl; C 2-10 alkynyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; R 3 R 4 NC 1-6 alkyl; R 3 R 4 NC (= O) -C 1-6 alkyl; R 3 O — C 1-6 alkyl; R 3 OC (= O) -C 1-6 alkyl; R 3 C (= O) -C 1-6 alkyl; R 3 C (= O) NR 3 -C 1-6 alkyl; R 3 R 4 NSO 2 —C 1-6 alkyl; R 3 CSO 2 N (R 4 ) -C 1-6 alkyl; R 3 R 4 NC (= O) N (R 5 ) -C 1-6 alkyl; R 3 R 4 NSO 2 N (R 5 ) -C 1-6 alkyl; aryl-C 1-6 alkyl; aryl-C (= O) -C 1-6 alkyl; heterocyclyl-C 1-6 alkyl; heterocyclyl-C (= O) -C 1-6 alkyl; substituted aryl-C 1-6 alkyl; substituted aryl-C (= O) -C 1-6 alkyl; substituted heterocyclyl-C 1-6 alkyl; substituted heterocyclyl-C (= O) -C 1-6 alkyl and C 1-10 hydrocarbylamino; R2 выбран из С1-6алкила, замещенного С1-6алкила, С2-6алкенила, замещенного С2-6алкенила, С2-6алкинила, замещенного С2-6алкинила, С3-6циклоалкила, замещенного С3-6циклоалкила, арила, замещенного арила, и С5-6гетероарила и замещенного С5-6гетероарила;R 2 is selected from C 1-6 alkyl, substituted C 1-6 alkyl, C 2-6 alkenyl, substituted C 2-6 alkenyl, C 2-6 alkynyl, substituted C 2-6 alkynyl, C 3-6 cycloalkyl, substituted C 3-6 cycloalkyl, aryl, substituted aryl, and C 5-6 heteroaryl and substituted C 5-6 heteroaryl; R3, R4 и R5 независимо выбраны из -Н, С1-6алкила, С2-6алкенила, С2-6алкинила и двухвалентной C1-6группы, которая вместе с другой двухвалентной С1-6группой образует часть кольца;R 3 , R 4 and R 5 are independently selected from —H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl and a divalent C 1-6 group, which together with another divalent C 1-6 group forms part of the ring; Х представляет собой С1-10двухвалентную группу, которая разделяет группы, присоединенные к ней, посредством одного или двух атомов;X represents a C 1-10 divalent group that separates the groups attached to it by one or two atoms; Ar представляет собой С4-12двухвалентную ароматическую группу; иAr represents a C 4-12 divalent aromatic group; and Y выбран из -СН= и -N=.Y is selected from —CH = and —N =. 2. Соединение по п.1, 2. The compound according to claim 1, где RF1 и RF2 независимо представляют собой С1-6алкил, замещенный одной или более чем одной группой, выбранной из -F, -Cl, -Br, -NO2, -CN, -ОН, -СНО, -C(=O)-R' и -OR', где R' представляет собой C1-3алкил.where R F1 and R F2 independently represent C 1-6 alkyl substituted with one or more than one group selected from —F, —Cl, —Br, —NO 2 , —CN, —OH, —CHO, —C ( = O) —R ′ and —OR ′, where R ′ is C 1-3 alkyl. 3. Соединение по п.1, 3. The compound according to claim 1, где RF1 и RF2 независимо выбраны из -CF3, -СН2CF3, -CH2CHF2, -CHFCF3, -CHFCHF2, -CHFCH2F, -CF2CF3, -CF2СН3, -CF2CH2F, -CF2CHF2, -CCl3, -СН2CCl3, -CH2CHCl2, -СН2CBr3, -СН2CHBr2, -CH2NO2, -CH2CH2NO2, -CH2CN, -CH2CH2CN и -СН2СН2OCH3.where R F1 and R F2 are independently selected from —CF 3 , —CH 2 CF 3 , —CH 2 CHF 2 , —CHFCF 3 , —CHFCHF 2 , —CHFCH 2 F, —CF 2 CF 3 , —CF 2 CH 3 , —CF 2 CH 2 F, —CF 2 CHF 2 , —CCl 3 , —CH 2 CCl 3 , —CH 2 CHCl 2 , —CH 2 CBr 3 , —CH 2 CHBr 2 , —CH 2 NO 2 , —CH 2 CH 2 NO 2 , —CH 2 CN, —CH 2 CH 2 CN, and —CH 2 CH 2 OCH 3 . 4. Соединение по п.1, где RF1 и RF2 независимо представляют собой С1-6группы, которые включают по меньшей мере 30% фтора по массе, и Z представляет собой O=.4. The compound according to claim 1, where R F1 and R F2 independently represent C 1-6 groups, which include at least 30% fluorine by weight, and Z represents O =. 5. Соединение по п.1, где R1 выбран из С1-10алкила; С1-10алкила, замещенного по меньшей мере одним галогеном, циано, ацетокси метилом и нитро; С2-10алкенила; С2-10алкенила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; С2-10алкинила; С2-10алкинила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; R3R4N-С1-6алкила; R3R4NC(=O)-С1-6алкила; R3O-С1-6алкила; R3OC(=O)-C1-6алкила; R3C(=O)-C1-6алкила; R3C(=O)NR3-C1-6алкила; R3R4NSO2-C1-6алкила; R3CSO2N(R4)-C1-6алкила; R3R4NC(=O)N(R5)-C1-6алкила; R3R4NSO2N(R5)-C1-6алкила; арил-С1-6алкила; арил-С(=O)-С1-6алкила; гетероциклил-С1-6алкила; гетероциклил-С(=O)-С1-6алкила; замещенного арил-С1-6алкила; замещенного арил-С(=O)-С1-6алкила; замещенного гетероциклил-С1-6алкила; замещенного гетероциклил-С(=O)-С1-6алкила и С1-10гидрокарбиламино;5. The compound according to claim 1, where R 1 selected from C 1-10 alkyl; C 1-10 alkyl substituted with at least one halogen, cyano, acetoxy methyl and nitro; C 2-10 alkenyl; C 2-10 alkenyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; C 2-10 alkynyl; C 2-10 alkynyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; R 3 R 4 N — C 1-6 alkyl; R 3 R 4 NC (= O) -C 1-6 alkyl; R 3 O — C 1-6 alkyl; R 3 OC (= O) -C 1-6 alkyl; R 3 C (= O) -C 1-6 alkyl; R 3 C (= O) NR 3 -C 1-6 alkyl; R 3 R 4 NSO 2 —C 1-6 alkyl; R 3 CSO 2 N (R 4 ) -C 1-6 alkyl; R 3 R 4 NC (= O) N (R 5 ) -C 1-6 alkyl; R 3 R 4 NSO 2 N (R 5 ) -C 1-6 alkyl; aryl-C 1-6 alkyl; aryl-C (= O) -C 1-6 alkyl; heterocyclyl-C 1-6 alkyl; heterocyclyl-C (= O) -C 1-6 alkyl; substituted aryl-C 1-6 alkyl; substituted aryl-C (= O) -C 1-6 alkyl; substituted heterocyclyl-C 1-6 alkyl; substituted heterocyclyl-C (= O) -C 1-6 alkyl and C 1-10 hydrocarbylamino; R2 выбран из C1-6алкила; C1-6алкила, замещенного по меньшей мере одним атомом фтора; С2-6алкенила; С2-6алкенила, замещенного по меньшей мере одним атомом фтора; С2-6алкинила; С2-6алкинила, замещенного по меньшей мере одним атомом фтора; С3-6циклоалкила; замещенного С3-6циклоалкила; арила; замещенного арила, и С5-6гетероарила и замещенного С5-6гетероарила;R 2 selected from C 1-6 alkyl; C 1-6 alkyl substituted with at least one fluorine atom; C 2-6 alkenyl; C 2-6 alkenyl substituted with at least one fluorine atom; C 2-6 alkynyl; C 2-6 alkynyl substituted with at least one fluorine atom; C 3-6 cycloalkyl; substituted C 3-6 cycloalkyl; aryl; substituted aryl, and C 5-6 heteroaryl and substituted C 5-6 heteroaryl; R3, R4 и R5 независимо выбраны из -Н, C1-6алкила, С2-6алкенила, С2-6алкинила и двухвалентной С1-6группы, которая вместе с другой двухвалентной С1-6группой образует часть кольца; иR 3 , R 4 and R 5 are independently selected from —H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl and a divalent C 1-6 group, which together with another divalent C 1-6 group forms part of the ring; and X выбран из -NR6-, -C(=O)-, -CH2-CH2-, -СН=СН-, -О-, -C(R6)(R7)- и -S(O)n-, в котором n представляет собой 0, 1 или 2, в которых R6 и R7 независимо представляют собой С1-6алкил, С2-6алкенил, С2-6алкинил, С1-6алкокси, -ОН или -Н.X is selected from —NR 6 -, —C (= O) -, —CH 2 —CH 2 -, —CH = CH—, —O—, —C (R 6 ) (R 7 ) -, and —S (O ) n -, in which n represents 0, 1 or 2, in which R 6 and R 7 independently represent C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, - OH or -H. 6. Соединение по п.1,6. The compound according to claim 1, где R1 выбран из С1-8алкила; С2-8алкенила; С2-8алкинила; арил-С1-6алкила; арил-С1-6алкила с арилом, замещенным по меньшей мере одной группой, выбранной из С1-6алкила, ацетоксиметила, нитро и галогена; R8R9N-С1-6алкила; R8OC1-6алкила; циклоалкил-С1-6алкила; гетероциклоалкил-С1-6алкила; гетероциклоалкил-С1-6алкила с гетероциклоалкилом, замещенным по меньшей мере одной группой, выбранной из С1-8алкила, ацетоксиметила, нитро и галогена; С1-6алкиларила; С1-6алкил-С(=O)-; С6-8арил-С(=O)-; С4-8гетероарил-С(=O)-; гетероарил-С1-6алкила; гетероарил-С1-6алкила с гетероарилом, замещенным по меньшей мере одной группой, выбранной из С1-6алкила, ацетоксиметила, нитро и галогена; и RNC1-6алкила;where R 1 selected from C 1-8 alkyl; C 2-8 alkenyl; C 2-8 alkynyl; aryl-C 1-6 alkyl; aryl-C 1-6 alkyl with aryl substituted by at least one group selected from C 1-6 alkyl, acetoxymethyl, nitro and halogen; R 8 R 9 N — C 1-6 alkyl; R 8 OC 1-6 alkyl; cycloalkyl-C 1-6 alkyl; heterocycloalkyl-C 1-6 alkyl; heterocycloalkyl-C 1-6 alkyl with heterocycloalkyl substituted with at least one group selected from C 1-8 alkyl, acetoxymethyl, nitro and halogen; C 1-6 alkylaryl; C 1-6 alkyl-C (= O) -; C 6-8 aryl-C (= O) -; C 4-8 heteroaryl-C (= O) -; heteroaryl-C 1-6 alkyl; heteroaryl-C 1-6 alkyl with heteroaryl substituted by at least one group selected from C 1-6 alkyl, acetoxymethyl, nitro and halogen; and R N C 1-6 alkyl; R2 выбран из -СН3, -СН2СН3, -СН(СН3)2, С3-6циклоалкила, -СН2CF2, -CHF2, -CF3 и арила;R 2 is selected from —CH 3 , —CH 2 CH 3 , —CH (CH 3 ) 2 , C 3-6 cycloalkyl, —CH 2 CF 2 , —CHF 2 , —CF 3, and aryl; RN представляет собой окисленный пиридил, в котором атом азота пиридильного кольца находится в окисленном состоянии (N+-O-);R N represents an oxidized pyridyl in which the nitrogen atom of the pyridyl ring is in an oxidized state (N + -O - ); Ar выбран из арилена; гетероарилена; арилена, замещенного по меньшей мере одной группой, выбранной из С1-6алкила, галогена, трифторметила, циано, нитро, гидрокси и С1-6алкокси; и гетероарилена, замещенного по меньшей мере одной группой, выбранной из С1-6алкила, галогена, трифторметила, циано, нитро, гидрокси и С1-6алкокси; иAr is selected from arylene; heteroarylene; arylene substituted with at least one group selected from C 1-6 alkyl, halogen, trifluoromethyl, cyano, nitro, hydroxy and C 1-6 alkoxy; and heteroarylene substituted with at least one group selected from C 1-6 alkyl, halogen, trifluoromethyl, cyano, nitro, hydroxy and C 1-6 alkoxy; and R8 и R9 независимо выбраны из -Н и С1-6алкила.R 8 and R 9 are independently selected from —H and C 1-6 alkyl. 7. Соединение по п.6, где арилен представляет собой пара-арилен; а гетероарилен выбран из пара-гетероарилена с шестичленным кольцом и мета-гетероарилена с пятичленным кольцом.7. The compound according to claim 6, where arylene is para-arylene; and heteroarylene is selected from para-heteroarylene with a six-membered ring and meta-heteroarylene with a five-membered ring. 8. Соединение по п.1, 8. The compound according to claim 1, где R1 выбран из этила, пропила, аллила, изопентила, бензила, диметиламиноэтила, 4-пиридилметила, 2-пиридилметила, 1-пирролилэтила, циклопропилметила, циклобутилметила, циклопентилметила, циклогексилметила, 2-пирролидилметила, 3-пирролидилметила, N-метил-2-пирролидилметила, N-метил-3-пирролидилметила, 2-пиперидилметила, 3-пиперидилметила, 4-пиперидилметила, N-метил-2-пиперидилметила, N-метил-3-пиперидилметила, N-метил-4-пиперидилметила, 3-тиенилметила, 2-тетрагидрофуранилметила, 3-тетрагидрофуранилметила, 2-тетрагидропиранилметила, 3-тетрагидропиранилметила, 4-тетрагидропиранилметила, (2-нитротиофен-5-ил)метила, (1-метил-1Н-имидазол-2-ил)метила, (5-(ацетоксиметил)-2-фуранил)метила, (2,3-дигидро-1Н-изоиндол-1-ил)метила и 5-(2-метилтиазолила);where R 1 is selected from ethyl, propyl, allyl, isopentyl, benzyl, dimethylaminoethyl, 4-pyridylmethyl, 2-pyridylmethyl, 1-pyrrolylethyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 2-pyrrolidylmethyl, 3-pyrrolidylmethyl -pyrrolidylmethyl, N-methyl-3-pyrrolidylmethyl, 2-piperidylmethyl, 3-piperidylmethyl, 4-piperidylmethyl, N-methyl-2-piperidylmethyl, N-methyl-3-piperidylmethyl, N-methyl-4-piperidylmethyl, 3-thienyl , 2-tetrahydrofuranylmethyl, 3-tetrahydrofuranylmethyl, 2-tetrahydropyranylmethyl, 3-tetrahydropyran ilmethyl, 4-tetrahydropyranylmethyl, (2-nitrothiophen-5-yl) methyl, (1-methyl-1H-imidazol-2-yl) methyl, (5- (acetoxymethyl) -2-furanyl) methyl, (2,3- dihydro-1H-isoindol-1-yl) methyl and 5- (2-methylthiazolyl); R2 выбран из -СН3, -СН2СН3, -СН(СН3)2, -CH2CF3, -CF3, циклопропила, циклобутила, циклопентила, циклогексила и фенила;R 2 is selected from —CH 3 , —CH 2 CH 3 , —CH (CH 3 ) 2 , —CH 2 CF 3 , —CF 3 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and phenyl; RF1 и RF2 представляют собой -CH2CF3, и Z представляет собой O=;R F1 and R F2 are —CH 2 CF 3 , and Z is O =; Ar выбран из пара-арилена; пара-арилена, замещенного С1-6алкилом, галогеном, трифторметилом, циано, нитро, гидрокси и С1-6алкокси; пара-гетероарилена с шестичленным кольцом; и пара-гетероарилена с шестичленным кольцом, замещенного группой, выбранной из С1-6алкила, галогена, трифторметила, циано, нитро, гидрокси и С1-6алкокси.Ar is selected from para-arylene; para-arylene substituted with C 1-6 alkyl, halogen, trifluoromethyl, cyano, nitro, hydroxy and C 1-6 alkoxy; six-membered para-heteroarylene; and six-membered para-heteroarylene substituted with a group selected from C 1-6 alkyl, halogen, trifluoromethyl, cyano, nitro, hydroxy and C 1-6 alkoxy. 9. Соединение по п.1,9. The compound according to claim 1, где RF1 и RF2 представляют собой -CH2CF3, и Z представляет собой O=;where R F1 and R F2 are —CH 2 CF 3 , and Z is O =; R2 представляет собой -СН2СН3;R 2 represents —CH 2 CH 3 ; Ar выбран из пара-фенилена и пара-пиридилена; иAr is selected from para-phenylene and para-pyridylene; and Х выбран из -СН2- и -СН(СН3)-.X is selected from —CH 2 - and —CH (CH 3 ) -. 10. Соединение по п.1, где указанное соединение выбрано из:10. The compound according to claim 1, where the specified compound is selected from: 2-[(4-Этоксифенил)метил]-1-(3-метилбутил)-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1- (3-methylbutyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 1-(Циклопропилметил)-2-[(4-этоксифенил)метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;1- (Cyclopropylmethyl) -2 - [(4-ethoxyphenyl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 1-(Циклогексилметил)-2-[(4-этоксифенил)метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;1- (Cyclohexylmethyl) -2 - [(4-ethoxyphenyl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(4-Этоксифенил)метил]-1-(2-фуранилметил)-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1- (2-furanylmethyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(4-Этоксифенил)метил]-1-[(2S)-2-пирролидинилметил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [(2S) -2-pyrrolidinylmethyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(4-Этоксифенил)метил]-1-[(2R)-2-пирролидинилметил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [(2R) -2-pyrrolidinylmethyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(4-этоксифенил)метил]-1-(4-пиридинилметил)-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-ethoxyphenyl) methyl] -1- (4-pyridinylmethyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[1-(4-Этоксифенил)этил]-1-(4-пиридинилметил)-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2- [1- (4-Ethoxyphenyl) ethyl] -1- (4-pyridinylmethyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(4-Этоксифенил)метил]-1-[(тетрагидро-2Н-пиран-4-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [(tetrahydro-2H-pyran-4-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide ; 2-[(4-Этоксифенил)метил]-1-[[(2R)-тетрагидро-2-фуранил]метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [[((2R) -tetrahydro-2-furanyl] methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide ; 2-[(4-Этоксифенил)метил]-1-[[(2S)-тетрагидро-2-фуранил]метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [[(2S) -tetrahydro-2-furanyl] methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide ; 2-[(4-Этоксифенил)метил]-1-[(тетрагидро-2Н-пиран-2-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [(tetrahydro-2H-pyran-2-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide ; 2-[(4-Этоксифенил)метил]-1-[(2R)-2-пиперидинилметил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [(2R) -2-piperidinylmethyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(5-Этокси-2-пиридил)метил]-1-[(тетрагидро-2Н-пиран-4-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(5-Ethoxy-2-pyridyl) methyl] -1 - [(tetrahydro-2H-pyran-4-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole -5-carboxamide; 2-[(5-Этокси-2-пиридинил)метил]-1-(3-метилбутил)-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(5-Ethoxy-2-pyridinyl) methyl] -1- (3-methylbutyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(4-Этоксифенил)метил]-1-[[(2R)-1-метил-2-пирролидинил]метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [[(2R) -1-methyl-2-pyrrolidinyl] methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5 β-carboxamide; 2-[(4-Этоксифенил)метил]-1-[[(2R)-1-метил-2-пиперидинил]метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(4-Ethoxyphenyl) methyl] -1 - [[(2R) -1-methyl-2-piperidinyl] methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5 β-carboxamide; 2-[(5-Этокси-2-пиридинил)метил]-1-[(2R)-2-пирролидинилметил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2 - [(5-Ethoxy-2-pyridinyl) methyl] -1 - [(2R) -2-pyrrolidinylmethyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[1-(4-Этоксифенил)этил]-1-[(2R)-2-пирролидинилметил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2- [1- (4-Ethoxyphenyl) ethyl] -1 - [(2R) -2-pyrrolidinylmethyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(5-Этокси-2-пиридинил)метил]-1-[[(2R)-1-метил-2-пиперидинил]метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(5-Ethoxy-2-pyridinyl) methyl] -1 - [[(2R) -1-methyl-2-piperidinyl] methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H -benzimidazole-5-carboxamide; 2-[(5-Этокси-2-пиридинил)метил]-1-[[(2R)-1-метил-2-пирролидинил]метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(5-Ethoxy-2-pyridinyl) methyl] -1 - [[(2R) -1-methyl-2-pyrrolidinyl] methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H -benzimidazole-5-carboxamide; 1-(Циклобутилметил)-2-(4-этоксибензил)-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;1- (Cyclobutylmethyl) -2- (4-ethoxybenzyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 1-(Циклобутилметил)-2-[(5-этоксипиридин-2-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;1- (Cyclobutylmethyl) -2 - [(5-ethoxypyridin-2-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 1-(Циклопентилметил)-2-[(5-этоксипиридин-2-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;1- (Cyclopentylmethyl) -2 - [(5-ethoxypyridin-2-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-(4-Этоксибензил)-1-[(2S)-пиперидин-2-илметил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2- (4-Ethoxybenzyl) -1 - [(2S) -piperidin-2-ylmethyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(5-Этоксипиридин-2-ил)метил]-1-(3-фурилметил)-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(5-Ethoxypyridin-2-yl) methyl] -1- (3-furylmethyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-[(5-Этоксипиридин-2-ил)метил]-1-(3-тиенилметил)-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(5-Ethoxypyridin-2-yl) methyl] -1- (3-thienylmethyl) -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 1-(Циклогексилметил)-2-[(5-этоксипиридин-2-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;1- (Cyclohexylmethyl) -2 - [(5-ethoxypyridin-2-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 1-(Циклогексилметил)-2-[(5-изопропоксипиридин-2-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;1- (Cyclohexylmethyl) -2 - [(5-isopropoxypyridin-2-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-(4-Этоксибензил)-1-[(4-метилморфолин-3-ил)метил]-N,N-бис(2,2,2-трифторэтил-1Н-бензимидазол-5-карбоксамида;2- (4-Ethoxybenzyl) -1 - [(4-methylmorpholin-3-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl-1H-benzimidazole-5-carboxamide; 2-[(5-Этоксипиридин-2-ил)метил]-1-[(4-метилморфолин-3-ил)метил]-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2 - [(5-Ethoxypyridin-2-yl) methyl] -1 - [(4-methylmorpholin-3-yl) methyl] -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazol-5 β-carboxamide; 2-(4-Этоксибензил)-1-{[(2S)-1-метилпиперидин-2-ил]метил}-N,N-бис(2,2,2-трифторэтил)-1H-бензимидазол-5-карбоксамида;2- (4-Ethoxybenzyl) -1 - {[(2S) -1-methylpiperidin-2-yl] methyl} -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; 2-(4-Изопропоксибензил)-1-{[(2R)-1-метилпиперидин-2-ил]метил}-N,N-бис(2,2,2-трифторэтил)-1Н-бензимидазол-5-карбоксамида;2- (4-Isopropoxybenzyl) -1 - {[(2R) -1-methylpiperidin-2-yl] methyl} -N, N-bis (2,2,2-trifluoroethyl) -1H-benzimidazole-5-carboxamide; и их фармацевтически приемлемых солей.and their pharmaceutically acceptable salts. 11. Соединение по любому из пп.1-10 для применения в качестве лекарства.11. The compound according to any one of claims 1 to 10 for use as a medicine. 12. Применение соединения по любому из пп.1-10 в производстве лекарства для лечения боли.12. The use of a compound according to any one of claims 1 to 10 in the manufacture of a medicament for the treatment of pain. 13. Применение соединения по любому из пп.1-10 в производстве лекарства для лечения рака.13. The use of a compound according to any one of claims 1 to 10 in the manufacture of a medicament for the treatment of cancer. 14. Применение соединения по любому из пп.1-10 в производстве лекарства для лечения рассеянного склероза, болезни Паркинсона, хореи Хантингтона, отторжения трансплантата или болезни Альцгеймера.14. The use of a compound according to any one of claims 1 to 10 in the manufacture of a medicament for the treatment of multiple sclerosis, Parkinson's disease, Huntington’s chorea, transplant rejection or Alzheimer's disease. 15. Фармацевтическая композиция, содержащая соединение по любому из пп.1-10 и фармацевтически приемлемый носитель.15. A pharmaceutical composition comprising a compound according to any one of claims 1 to 10 and a pharmaceutically acceptable carrier. 16. Способ лечения боли у теплокровного животного, включающий стадию введения указанному животному, нуждающемуся в подобном лечении, терапевтически эффективного количества соединения по любому из пп.1-10.16. A method of treating pain in a warm-blooded animal, comprising the step of administering to said animal in need of such treatment a therapeutically effective amount of a compound according to any one of claims 1 to 10. 17. Способ получения соединения, включающий стадию взаимодействия соединения, представленного формулой (II)17. A method for producing a compound, comprising the step of reacting a compound represented by formula (II)
Figure 00000002
Figure 00000002
 где RF1 и RF2 независимо представляют собой электроноакцепторные группы;where R F1 and R F2 independently represent electron withdrawing groups; Z выбран из O= и S=;Z is selected from O = and S =; R1 выбран из С1-10алкила; С1-10алкила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; С2-10алкенила; С2-10алкенила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; С2-10алкинила; С2-10алкинила, замещенного по меньшей мере одним галогеном, циано, ацетоксиметилом и нитро; R3R4N-C1-6алкила; R3R4NC(=O)-С1-6алкила; R3O-С1-6алкила; R3OC(=O)-C1-6алкила; R3C(=O)-С1-6алкила; R3C(=O)NR3-С1-6алкила; R3R4NSO2-C1-6алкила; R3CSO2N(R4)-C1-6алкила; R3R4NC(=O)N(R5)-С1-6алкила; R3R4NSO2N(R5)-C1-6алкила; арил-С1-6алкила; арил-С(=O)-С1-6алкила; гетероциклил-С1-6алкила; гетероциклил-С(=O)-С1-6алкила; замещенного арил-С1-6алкила; замещенного арил-С(=O)-С1-6алкила; замещенного гетероциклил-С1-6алкила; замещенного гетероциклил-С(=O)-С1-6алкила и C1-10гидрокарбиламино;R 1 selected from C 1-10 alkyl; C 1-10 alkyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; C 2-10 alkenyl; C 2-10 alkenyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; C 2-10 alkynyl; C 2-10 alkynyl substituted with at least one halogen, cyano, acetoxymethyl and nitro; R 3 R 4 NC 1-6 alkyl; R 3 R 4 NC (= O) -C 1-6 alkyl; R 3 O — C 1-6 alkyl; R 3 OC (= O) -C 1-6 alkyl; R 3 C (= O) -C 1-6 alkyl; R 3 C (= O) NR 3 -C 1-6 alkyl; R 3 R 4 NSO 2 —C 1-6 alkyl; R 3 CSO 2 N (R 4 ) -C 1-6 alkyl; R 3 R 4 NC (= O) N (R 5 ) -C 1-6 alkyl; R 3 R 4 NSO 2 N (R 5 ) -C 1-6 alkyl; aryl-C 1-6 alkyl; aryl-C (= O) -C 1-6 alkyl; heterocyclyl-C 1-6 alkyl; heterocyclyl-C (= O) -C 1-6 alkyl; substituted aryl-C 1-6 alkyl; substituted aryl-C (= O) -C 1-6 alkyl; substituted heterocyclyl-C 1-6 alkyl; substituted heterocyclyl-C (= O) -C 1-6 alkyl and C 1-10 hydrocarbylamino; R2 выбран из C1-6алкила, замещенного C1-6алкила, С2-6алкенила, замещенного С2-6алкенила, С2-6алкинила, замещенного С2-6алкинила, С3-6циклоалкила, замещенного С3-6циклоалкила, арила, замещенного арила, и С5-6гетероарила и замещенного С5-6гетероарила;R 2 is selected from C 1-6 alkyl, substituted C 1-6 alkyl, C 2-6 alkenyl, substituted C 2-6 alkenyl, C 2-6 alkynyl, substituted C 2-6 alkynyl, C 3-6 cycloalkyl, substituted C 3-6 cycloalkyl, aryl, substituted aryl, and C 5-6 heteroaryl and substituted C 5-6 heteroaryl; R3, R4 и R5 независимо выбраны из -Н, С1-6алкила, С2-6алкенила, С2-6алкинила и двухвалентной С1-6группы, которая вместе с другой двухвалентной С1-6группой образует часть кольца;R 3 , R 4 and R 5 are independently selected from —H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl and a divalent C 1-6 group, which together with another divalent C 1-6 group forms part of the ring; Х представляет собой С1-10двухвалентную группу, которая разделяет группы, присоединенные к ней, посредством одного или двух атомов;X represents a C 1-10 divalent group that separates the groups attached to it by one or two atoms; А выбран из -ОН, -Cl, -Br и -I;A is selected from —OH, —Cl, —Br, and —I; Ar представляет собой С4-12двухвалентную ароматическую группу; иAr represents a C 4-12 divalent aromatic group; and Y выбран из -СН= и -N=,Y is selected from —CH = and —N =, с R2OArXCOA.with R 2 OArXCOA. 18. Способ получения соединения, включающий стадию взаимодействия соединения, представленного формулой (III)18. A method for producing a compound, comprising the step of reacting a compound represented by formula (III)
Figure 00000003
Figure 00000003
 где r и s выбраны из 0, 1 и 2;where r and s are selected from 0, 1 and 2; R10 выбран из С1-6алкилена, -О- и -NR11-, где R11 представляет собой С1-6алкил;R 10 is selected from C 1-6 alkylene, —O— and —NR 11 -, where R 11 is C 1-6 alkyl; RF1 и RF2 независимо представляют собой электроноакцепторные группы;R F1 and R F2 independently represent electron withdrawing groups; Х представляет собой С1-10двухвалентную группу, которая разделяет группы, присоединенные к ней, посредством одного или двух атомов;X represents a C 1-10 divalent group that separates the groups attached to it by one or two atoms; Ar представляет собой С4-12двухвалентную ароматическую группу;Ar represents a C 4-12 divalent aromatic group; R2 выбран из С1-6алкила, замещенного С1-6алкила, С2-6алкенила, замещенного С2-6алкенила, С2-6алкинила, замещенного С2-6алкинила, С3-6циклоалкила, замещенного С3-6циклоалкила, арила, замещенного арила, и С5-6гетероарила и замещенного С5-6гетероарила; иR 2 is selected from C 1-6 alkyl, substituted C 1-6 alkyl, C 2-6 alkenyl, substituted C 2-6 alkenyl, C 2-6 alkynyl, substituted C 2-6 alkynyl, C 3-6 cycloalkyl, substituted C 3-6 cycloalkyl, aryl, substituted aryl, and C 5-6 heteroaryl and substituted C 5-6 heteroaryl; and Y выбран из -СН= и -N=, с формальдегидом.Y is selected from —CH = and —N =, with formaldehyde.
RU2005109156/04A 2002-10-16 2003-10-15 Novel derivatives of benzimidazole, methods for their preparing, their using and pharmaceutical composition containing thereof RU2323211C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE0203070A SE0203070D0 (en) 2002-10-16 2002-10-16 Novel compounds
SE0203070-8 2002-10-16

Publications (2)

Publication Number Publication Date
RU2005109156A true RU2005109156A (en) 2006-01-20
RU2323211C2 RU2323211C2 (en) 2008-04-27

Family

ID=20289294

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2005109156/04A RU2323211C2 (en) 2002-10-16 2003-10-15 Novel derivatives of benzimidazole, methods for their preparing, their using and pharmaceutical composition containing thereof

Country Status (20)

Country Link
US (1) US7407968B2 (en)
EP (1) EP1554254A1 (en)
JP (1) JP2006505568A (en)
KR (1) KR20050049551A (en)
CN (1) CN100349874C (en)
AR (1) AR041626A1 (en)
AU (1) AU2003269775B2 (en)
BR (1) BR0315320A (en)
CA (1) CA2501418A1 (en)
IS (1) IS7827A (en)
MX (1) MXPA05003901A (en)
NO (1) NO20052182L (en)
NZ (1) NZ539079A (en)
PL (1) PL376564A1 (en)
RU (1) RU2323211C2 (en)
SE (1) SE0203070D0 (en)
TW (1) TWI285638B (en)
UA (1) UA81919C2 (en)
WO (1) WO2004035548A1 (en)
ZA (1) ZA200502928B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE0101387D0 (en) * 2001-04-20 2001-04-20 Astrazeneca Ab Novel compounds
SE0203070D0 (en) 2002-10-16 2002-10-16 Astrazeneca Ab Novel compounds
SE0301698D0 (en) 2003-06-10 2003-06-10 Astrazeneca Ab Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
SE0301701D0 (en) * 2003-06-10 2003-06-10 Astrazeneca Ab Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
SE0301699D0 (en) * 2003-06-10 2003-06-10 Astrazeneca Ab Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
JP2008518905A (en) * 2004-11-02 2008-06-05 ファイザー株式会社 Sulfonylbenzimidazole derivatives
WO2007091950A1 (en) * 2006-02-07 2007-08-16 Astrazeneca Ab Benzimidazoles and imidazopyridines useful in the treatment of diseases or disorders associated with cannabinoid receptor 2 (cb2) such as pain
CN101511796B (en) 2006-09-05 2012-05-09 协和发酵麒麟株式会社 Imidazole derivative
US8236841B2 (en) 2006-09-13 2012-08-07 Kyowa Hakko Kirin Co., Ltd. Fused heterocycle derivative
MY146924A (en) 2007-06-21 2012-10-15 Cara Therapeutics Inc Substituted imidazoheterocycles
US20120004222A1 (en) * 2007-08-21 2012-01-05 Zhicai Wu Cb2 receptor ligands for the treatment of pain
US8759535B2 (en) 2010-02-18 2014-06-24 High Point Pharmaceuticals, Llc Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
EP2734517B1 (en) * 2011-07-18 2017-08-30 Merck Patent GmbH Benzamides
JP2015530360A (en) 2012-07-13 2015-10-15 ザ クリーブランド クリニック ファウンデーションＴｈｅ Ｃｌｅｖｅｌａｎｄ ＣｌｉｎｉｃＦｏｕｎｄａｔｉｏｎ Neuroprotective CB2 receptor agonist
WO2016089648A1 (en) 2014-12-01 2016-06-09 Vtv Therapeutics Llc Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof
CN111658644B (en) * 2020-03-31 2021-05-14 中山大学 Small-molecule STAT3 inhibitor WZ-2-033 and application thereof in preparation of medicines for treating breast cancer and gastric cancer

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2945044A (en) 1957-07-12 1960-07-12 Ciba Pharm Prod Inc Certain 1-(diethyl-aminoethyl), 5-amino, 2-benzyl or substituted benzyl, benzimidazoles
FR1481049A (en) * 1965-11-25 1967-05-19 France Ministre Des Armees New 5-substituted dialkylaminoalkyl-1 p-alkoxyphenyl-2-alkylbenzimidazoles
CA2036307C (en) * 1990-03-08 2002-07-09 Susan Jean Ward 3-arylcarbonyl-1-aminoalkyl-1h-indole-containing antiglaucoma compositions and method
FR2741621B1 (en) 1995-11-23 1998-02-13 Sanofi Sa NOVEL PYRAZOLE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
FR2789079B3 (en) 1999-02-01 2001-03-02 Sanofi Synthelabo PYRAZOLECARBOXYLIC ACID DERIVATIVE, ITS PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
AUPR118000A0 (en) * 2000-11-02 2000-11-23 Amrad Operations Pty. Limited Therapeutic molecules and methods
JP2005503998A (en) 2001-01-29 2005-02-10 ユニバーシティ オブ コネチカット Receptor-selective cannabi mimetic aminoalkylindoles
SE0101387D0 (en) * 2001-04-20 2001-04-20 Astrazeneca Ab Novel compounds
WO2003053938A1 (en) * 2001-12-20 2003-07-03 Novo Nordisk A/S Benzimidazols and indols as glucagon receptor antagonists/inverse agonisten
SE0203070D0 (en) 2002-10-16 2002-10-16 Astrazeneca Ab Novel compounds

Also Published As

Publication number Publication date
KR20050049551A (en) 2005-05-25
TWI285638B (en) 2007-08-21
US20070105893A1 (en) 2007-05-10
BR0315320A (en) 2005-08-16
US7407968B2 (en) 2008-08-05
AU2003269775B2 (en) 2007-05-03
RU2323211C2 (en) 2008-04-27
TW200410944A (en) 2004-07-01
CN1726194A (en) 2006-01-25
EP1554254A1 (en) 2005-07-20
PL376564A1 (en) 2006-01-09
CN100349874C (en) 2007-11-21
IS7827A (en) 2005-04-27
SE0203070D0 (en) 2002-10-16
MXPA05003901A (en) 2005-06-22
AR041626A1 (en) 2005-05-26
ZA200502928B (en) 2006-02-22
CA2501418A1 (en) 2004-04-29
NZ539079A (en) 2007-11-30
JP2006505568A (en) 2006-02-16
AU2003269775A1 (en) 2004-05-04
UA81919C2 (en) 2008-02-25
NO20052182L (en) 2005-05-03
WO2004035548A1 (en) 2004-04-29

Similar Documents

Publication Publication Date Title
RU2005109156A (en) NEW COMPOUNDS
RU2447060C2 (en) Sphyngosine kinase inhibitors
US20160101109A1 (en) Method of treating arthritis
RU2219167C2 (en) N-substituted aminotetralines as ligands for receptor of y5 of neuropeptide y useful in treatment of obesity and other disorders
RU2003129638A (en) NEW COMPOUNDS
RU2495873C2 (en) New uracil compound or salt thereof possessing human deoxyuridine triphosphatase
RU2006134020A (en) CONDENSED PYRAZOLE DERIVATIVES
RU2003132687A (en) TREATMENT OF TYPE 2 DIABETES BY DIPEPTIDYLPEPTIDASE IV INHIBITORS
KR910007918A (en) Substituted 5-[(tetrazolyl) alkenyl] imidazole
RU2003134544A (en) AMRIDES OF ANTRANILIC ACID, METHODS FOR PRODUCING THEM, THEIR APPLICATION AS ANTIARRHYTHMIC MEDICINES, AND ALSO CONTAINING THEIR PHARMACEUTICAL COMPOSITIONS
RU2007137668A (en) 39-DESMETOXY DERIVATIVES
JP2008518969A5 (en)
KR900701782A (en) Quinuclidin Therapeutics
KR920014805A (en) Quinazolinone compounds, pharmaceutical compositions thereof and methods for their preparation
DE69219008T2 (en) Pyrimidine derivatives, their methods of preparation, the intermediates obtained, their use as medicinal products and pharmaceutical compositions containing them
JP2011512331A5 (en)
RU2001130163A (en) Derivatives of piperidine and a pharmaceutical composition based on them
JP2001526218A5 (en)
RU2008146383A (en) DIALKYLPHENYLIC DERIVATIVES HAVING AGONISTIC ACTIVITY AGAINST β2-ADRENERGIC RECEPTORS AND ANTAGONISTIC ACTIVITY AGAINST MUSCARINE RECEPTORS
JP7416757B2 (en) Substituted tetrahydrocyclopenta[c]pyrroles, substituted dihydropyrrolidines, analogs thereof, and methods of using them
RU95113148A (en) Derivative of 2-(2-amino-1,6-dihydro-6-oxopurine-9-yl)-methoxy- -1,3-propanediol
JPH01279887A (en) 6-substituted purinylpiperadine derivative
KR970706279A (en) Benzopyran and benzo-condensed compounds, their preparation and their use as leukotriene B4 (LTB4) antagonists (BENZOPYRAN AND BENZO-FUSED COMPOUNDS, THEIR PREPARATION AND THEIR USE AS LEUKOTRIENE B4 (LTB4) ANTAGONISTS)
JP3214856B2 (en) Imidazolyl-alkenoic acid
RU2002130247A (en) OXADIAZOLE DERIVATIVES WITH ANTITUMER ACTION

Legal Events

Date Code Title Description
MM4A The patent is invalid due to non-payment of fees

Effective date: 20081016